Der A2+‐Mechanismus der säurekatalytischen Hydrolyse von Epoxiden und anderen cyklischen Oxa‐ Verbindungen | Zendy

Willi Alfred V. | Zendy

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Der A2+‐Mechanismus der säurekatalytischen Hydrolyse von Epoxiden und anderen cyklischen Oxa‐ Verbindungen

Author(s) -

Willi Alfred V.

Publication year - 1973

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19730560635

Subject(s) - chemistry , carbonium ion , epoxide , protonation , catalysis , acid catalysis , medicinal chemistry , solvent , hydrolysis , stereochemistry , ion , organic chemistry

It is suggested that the acid catalyzed hydrolyses of isobutene oxide and propene oxide proceed via rate‐determining bimolecular reaction between a carbonium ion and solvent water (A2 + mechanism). The carbonium ion is formed by ring opening of the protonated epoxide, in a relatively fast preceding step. This mechanism is in agreement with all experimental facts known today. There is evidence for a similar mechanism in the acid catalyzed hydrolyses of cyclic acetals.

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